Director, Dragons
WFA Digital Insight
The demand for strategic leaders in the digital space is on the rise, with a 25% increase in related job postings in the last year. Gainsight is at the forefront of this trend, leveraging AI to drive customer success. As a leader in this field, you'll need to be well-versed in strategic planning, stakeholder management, and operational execution. Gainsight's commitment to innovation and customer-centricity makes this role an exciting opportunity for those who thrive in fast-paced, dynamic environments. With the remote job market continuing to grow, candidates who can adapt and lead in this space will be highly sought after. Before applying, consider your experience in driving cross-functional initiatives and your ability to communicate complex ideas to executive leadership.
Job Description
About the Role
The Director, Dragons role at Gainsight is a strategic leadership position that will drive company-wide strategy and operational excellence. This role will be responsible for owning and continuously improving the company's core operating cadence, including quarterly business reviews, V2MOM/OKR setting, mid-cycle tracking, end-of-cycle reporting, and executive team rhythms. As a key member of the Corporate Services team, you will report to the VP, Strategy & Business Operations and work closely with executive leadership to drive high-priority, cross-functional strategic initiatives.As a seasoned leader, you will thrive in a high-impact, ambiguous environment and enjoy working cross-functionally with teams like the CEO, CFO, CRO, Corporate Marketing, and Business Unit GMs. Your strong skills in strategic planning, stakeholder management, and operational execution will be essential in driving the company's growth and success.
What You Will Do
- Own and continuously improve the company's core operating cadence, including quarterly business reviews, V2MOM/OKR setting, mid-cycle tracking, end-of-cycle reporting, and executive team rhythms
- Drive high-priority, cross-functional strategic initiatives on behalf of the CEO, acting as program manager with end-to-end accountability for coordination, stakeholder alignment, and delivery
- Coordinate the annual planning process end-to-end in partnership with Finance, translating strategic priorities into resource and investment decisions for CEO and CFO review
- Own the narrative and coordination for board decks, investor materials, and key executive presentations, ensuring the CEO is prepared and aligned for high-stakes internal and external moments
- Build and maintain the data layer that supports executive decision-making, including performance dashboards, KPI tracking, and business reviews synthesizing cross-functional data for the CEO and CFO
- Serve as a shared strategic resource to the Business Unit GMs and functional leaders, supporting cross-functional coordination and ensuring executive visibility on issues that span organizational boundaries
- Provide analytical and project management support on M&A or strategic partnership evaluations as needed
- Develop and maintain strong relationships with executive leadership and other key stakeholders to ensure alignment and effective communication
What We Are Looking For
- 3+ years of relevant experience and a Bachelor's degree (or equivalent combination of education and experience)
- Experience in private equity / venture capital, strategy, business operations, management consulting, or a Chief of Staff role, with demonstrated ability to drive complex, cross-functional work in a fast-moving environment
- Strong structured thinking and communication skills, with the ability to synthesize ambiguous information into clear recommendations and crisp executive-ready materials
- High degree of analytical fluency, including comfort building financial models, synthesizing data from multiple sources, and translating analysis into executive-level insights
- Proficiency in data analysis and visualization tools, as well as Excel and PowerPoint; able to build and present executive-grade materials independently
- Strong executive presence and interpersonal skills, with the ability to build and maintain effective relationships with executive leadership and other key stakeholders
Nice to Have
- Experience working in a remote environment, with a strong ability to self-motivate and work independently
- Familiarity with AI-powered customer success platforms and tools
- Experience in the digital marketing or tech industry, with a strong understanding of the current trends and challenges
Benefits and Perks
- Competitive salary and benefits package
- Opportunity to work with a leading company in the customer success space
- Collaborative and dynamic work environment
- Professional development and growth opportunities
- Flexible work arrangements, including remote work options
- Access to cutting-edge technology and tools
- Recognition and rewards for outstanding performance
- Comprehensive health and wellness benefits
- Generous paid time off and holiday schedule
- 401(k) or retirement savings plan
- Employee discount programs and other perks
How to Stand Out
- Develop a strong understanding of the company's products and services, as well as the current market trends and challenges in the customer success space.
- Be prepared to discuss your experience working in a fast-paced, dynamic environment, and how you handle ambiguity and change.
- Highlight your skills in strategic planning, stakeholder management, and operational execution, and be prepared to provide specific examples of how you've applied these skills in previous roles.
- Make sure your resume and online profiles are up-to-date and showcase your experience and skills in a clear and concise manner.
- Research the company culture and values, and be prepared to discuss how you align with them and how you can contribute to the team's success.
- Practice your communication and presentation skills, as you will be working closely with executive leadership and other key stakeholders.
- Be prepared to discuss your experience working in a remote environment, and how you stay motivated and engaged while working independently.
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